Chemical. CAS 83-79-4. Formula C23H22O6. MW 394.4. Synthetic. Originally isolated from Lonchocarpus nicou. Cell-permeable reversible and competitive mitochondrial electron transport chain complex I NADH-CoQ reductase inhibitor IC50=1.7-2.2µM. Inhibits NADH/DB oxidoreductase and NADH oxidase and consequently oxidative phosphorylation OXPHOS. Specifically inhibits NAD-linked substrate oxidation of NADH dehydrogenase. Useful agent for immunometabolism research. Inhibition of electron transport chain in mitochondria leads to blocking of the transfer of electrons from iron-sulfur centers in complex I to ubiquinone. This interferes with NADH during the creation of usable cellular energy ATP, and Complex I is unable to pass off its electron to CoQ, creating a back-up of electrons within the mitochondrial matrix. Cellular oxygen is reduced to the radical, creating reactive oxygen species, which can damage DNA and other components of the mitochondria.